Allylsilanes have become indispensable in synthesis as reactants in carbon-carbon bond forming transformations. Bridgehead allylsilanes are a recent but un-studied sub-class of these important intermediates. The proposal includes an outline for investigating the carbon-carbon bond forming reactions of bridgehead allylsilanes. The novel stereoelectronic environment of these compounds will be utilized to direct electrophiles in asymmetric reactions. The mechanistic knowledge gained through these investigations will expand upon current understanding of allylsilane reactivity. Additionally, a demonstration of the utility of bridgehead allylsilanes in synthesis will be pursued in an approach to the natural product, Upial. [unreadable] [unreadable]